3',4'-Dehydrovinblastine → methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate

HRID 2059358

反応式

HRID 2059358 の反応式
[CH3:1][CH2:2][C:3]1[CH2:14][N:12]2[CH2:13][C@H:5]([CH2:6][C@:7]([C:55]([O:57][CH3:58])=[O:56])([C:22]3[CH:27]=[C:26]4[C:28]56[C@@H:39]([N:40]([CH3:41])[C:25]4=[CH:24][C:23]=3[O:53][CH3:54])[C@@:38]([OH:46])([C:42]([O:44][CH3:45])=[O:43])[C@H:37]([O:47][C:48]([CH3:50])=[O:49])[C@:33]3([CH2:51][CH3:52])[CH:34]=[CH:35][CH2:36][N:31]([C@H:32]53)[CH2:30][CH2:29]6)[C:8]3[NH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:9]=3[CH2:10][CH2:11]2)[CH:4]=1.C(Cl)(Cl)Cl.C[OH:64]>C(Cl)(Cl)Cl>[CH3:1][CH2:2][C@@:3]12[O:64][C@@H:4]1[C@H:5]1[CH2:13][N:12]([CH2:11][CH2:10][C:9]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=4[NH:21][C:8]=3[C@@:7]([C:55]([O:57][CH3:58])=[O:56])([C:22]3[CH:27]=[C:26]4[C@:28]56[C@@H:32]7[C@:33]([CH2:51][CH3:52])([C@@H:37]([O:47][C:48]([CH3:50])=[O:49])[C@:38]([OH:46])([C:42]([O:44][CH3:45])=[O:43])[C@@H:39]5[N:40]([CH3:41])[C:25]4=[CH:24][C:23]=3[O:53][CH3:54])[CH:34]=[CH:35][CH2:36][N:31]7[CH2:30][CH2:29]6)[CH2:6]1)[CH2:14]2

参加物

4

反応物 2

HCID 1511203',4'-DehydrovinblastineHCID 21584188Chloroform methanol

生成物 1

HCID 442111methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-methoxycarbonyl-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraene-13-carboxylate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of 50 mg of "anhydrovinblastine" III in 3 cm3 of chloroform at ambient temperature (20° C.) is stirred in the air in the presence of 50 mg of silica for 72 hours then diluted with 20 cm3 of chloroform/methanol 85/15 mixture, filtered and evaporated under reduced pressure. The mixture obtained is purified by chromatography on a thick layer of silica under the same conditions as in Example 1 and provides 13.8 mg of leurosine I and 20 mg of "anhydrovinblastine" III which may be recycled.

後処理

  1. filtrationfiltered
  2. customevaporated under reduced pressure
  3. customThe mixture obtained
  4. customis purified by chromatography on a thick layer of silica under the same conditions as in Example 1

出典と根拠

ORDレコード
ord-86c290a5fea04f208329b0096d8f67ff
出典データセット
uspto-grants-1982_03
特許番号
US04322350

関連ノート

読み込み中…